EP1221845B1 - Active ingredient combinations having insecticidal and acaricidal properties - Google Patents

Description

The present invention relates to new combinations of active ingredients which consist of a known cyclic ketoenol on the one hand and other known insecticides Active ingredients, on the other hand, exist and have very good insecticidal and acaricidal properties have.

It is already known that certain cyclic ketoenols are used to combat animal pests, such as insects and unwanted acarids can (see EP-A-528 156). The effectiveness of these substances is good, but it does not low application rates left something to be desired in some cases.

Furthermore, it has become known that agonists and antagonists of Nicotinergic acetylcholine receptors can be used to control insects.

in welcher

X'

für C₁-C₆-Alkyl, Halogen, C₁-C₆-Alkoxy oder C₁-C₃-Halogenalkyl steht,

Y'

für Wasserstoff, C₁-C₆-Alkyl, Halogen, C₁-C₆-Alkoxy, C₁-C₃-Halogenalkyl steht,

Z'

für C₁-C₆-Alkyl, Halogen, C₁-C₆-Alkoxy steht,

n

für eine Zahl von 0-3 steht,

A' und B'

gleich oder verschieden sind und fiir Wasserstoff oder gegebenenfalls durch Halogen substituiertes geradkettiges oder verzweigtes C₁-C₁₂-Alkyl, C₃-C₈-Alkenyl, C₃-C₈-Alkinyl, C₁-C₁₀-Alkoxy-C₂-C₈-alkyl, C₁-C₈-Polyalkoxy-C₂-C₈-alkyl, C₁-C₁₀-Alkylthio-C₂-C₈-alkyl, Cycloalkyl mit 3-8 Ringatomen, das durch Sauerstoff und/oder Schwefel unterbrochen sein kann und gegebenenfalls durch Halogen, C₁-C₆-Alkyl, C₁-C₆-Halogenalkyl-, C₁-C₆-Alkoxy-, C₁-C₆-Halogenalkoxy, Nitro substituiertes Phenyl oder Phenyl-C₁-C₆-alkyl steht,

oder worin

A' und B'

gemeinsam mit dem Kohlenstoffatom, an das sie gebunden sind einen gesättigten oder ungesättigten, gegebenenfalls durch Sauerstoff und/oder Schwefel unterbrochenen und gegebenenfalls durch Halogen, C₁-C₆-Alkyl, C₁-C₆-Alkoxy, C₁-C₄-Halogenalkyl, C₁-C₄-Halogenalkoxy, C₁-C₄-Alkylthio oder gegebenenfalls substituiertes Phenyl substituierten oder gegebenenfalls benzokondensierten 3- bis 8-gliedrigen Ring bilden,

G'

für Wasserstoff (a) oder für die Gruppen

steht, in welchen

R¹

für gegebenenfalls durch Halogen substituiertes: C₁-C₂₀-Alkyl, C₂-C₂₀-Alkenyl, C₁-C₈-Alkoxy-C₂-C₈-alkyl, C₁-C₈-Alkylthio-C₂-C₈-alkyl, C₁-C₈-Polyalkoxy-C₂-C₈-alkyl oder Cycloalkyl mit 3-8 Ringatomen, das durch Sauerstoff- und/oder Schwefelatome unterbrochen sein kann, steht,
für gegebenenfalls durch Halogen, Nitro, C₁-C₆-Alkyl, C₁-C₆-Alkoxy, C₁-C₆-Halogenalkyl, C₁-C₆-Halogenalkoxy-substituiertes Phenyl steht;
für gegebenenfalls durch Halogen-, C₁-C₆-Alkyl, C₁-C₆-Alkoxy-, C₁-C₆-Halogenalkyl-, C₁-C₆-Halogenalkoxy-substituiertes Phenyl-C₁-C₆-alkyl steht,
für gegebenenfalls durch Halogen und/oder C₁-C₆-Alkyl substituiertes Pyridyl, Pyrimidyl, Thiazolyl und Pyrazolyl steht,
für gegebenenfalls durch Halogen und/oder C₁-C₆-Alkyl-substituiertes Phenoxy-C₁-C₆-alkyl steht,

R²

für gegebenenfalls durch Halogen substituiertes: C₁-C₂₀-Alkyl, C₂-C₂₀-Alkenyl, C₁-C₈-Alkoxy-C₂-C₈-alkyl, C₁-C₈-Polyalkoxy-C₂-C₈-alkyl steht,
für gegebenenfalls durch Halogen, Nitro, C₁-C₆-Alkyl, C₁-C₆-Alkoxy, C₁-C₆-Halogenalkyl-substituiertes Phenyl oder Benzyl steht,

R³, R⁴ und R⁵

unabhängig voneinander für gegebenenfalls durch Halogen substituiertes C₁-C₈-Alkyl, C₁-C₈-Alkoxy, C₁-C₈-Alkylamino, Di-(C₁-C₈)-Alkylamino, C₁-C₈-Alkylthio, C₂-C₅-Alkenylthio, C₂-C₅-Alkinylthio, C₃-C₇-Cycloalkylthio, für gegebenenfalls durch Halogen, Nitro, Cyano, C₁-C₄-Alkoxy, C₁-C₄-Halogenalkoxy, C₁-C₄-Alkylthio, C₁-C₄-Halogen-alkylthio, C₁-C₄-Alkyl, C₁-C₄-Halogenalkyl substituiertes Phenyl, Phenoxy oder Phenylthio stehen,

R⁶ und R⁷

unabhängig voneinander für gegebenenfalls durch Halogen substituiertes C₁-C₂₀-Alkyl, C₁-C₂₀-Alkoxy, C₂-C₈-Alkenyl, C₁-C₂₀-Alkoxy-C₁-C₂₀-alkyl, für gegebenenfalls durch Halogen, C₁-C₂₀-Halogenalkyl, C₁-C₂₀-Alkyl oder C₁-C₂₀-Alkoxy substituiertes Phenyl, fiir gegebenenfalls durch Halogen, C₁-C₂₀-Alkyl, C₁-C₂₀-Halogenalkyl oder C₁-C₂₀-Alkoxy substituiertes Benzyl steht oder zusammen für einen gegebenenfalls durch Sauerstoff unterbrochenen C₂-C₆-Alkylenring stehen,

und mindestens einem Agonisten bzw. Antagonisten von Acetylcholinrezeptoren der Formel (II) synergistisch wirksam sind und sich zur Bekämpfung tierischer Schädlinge eignen. Aufgrund dieses Synergismus können deutlich geringere Wirkstoffmengen verwendet werden, d.h. die Wirkung der Mischung ist größer als die Wirkung der Einzelkomponenten.It has now been found that mixtures of cyclic ketoenols of the formula (I)

in which

X '

represents C ₁ -C ₆ alkyl, halogen, C ₁ -C ₆ alkoxy or C ₁ -C ₃ haloalkyl,

Y '

represents hydrogen, C ₁ -C ₆ alkyl, halogen, C ₁ -C ₆ alkoxy, C ₁ -C ₃ haloalkyl,

Z '

represents C ₁ -C ₆ alkyl, halogen, C ₁ -C ₆ alkoxy,

n

represents a number from 0-3,

A 'and B'

are identical or different and are hydrogen or straight-chain or branched C ₁ -C ₁₂ alkyl which is optionally substituted by halogen, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, C ₁ -C ₁₀ alkoxy-C ₂ - C ₈ alkyl, C ₁ -C ₈ polyalkoxy-C ₂ -C ₈ alkyl, C ₁ -C ₁₀ alkylthio-C ₂ -C ₈ alkyl, cycloalkyl with 3-8 ring atoms, which is caused by oxygen and / or Sulfur can be interrupted and optionally substituted by halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, nitro or phenyl-C ₁ -C ₆ alkyl,

or in what

A 'and B'

together with the carbon atom to which they are attached a saturated or unsaturated one which is optionally interrupted by oxygen and / or sulfur and optionally by halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₄ - haloalkyl, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ alkylthio unsubstituted or optionally substituted phenyl or optionally benzo-fused 3- to 8-membered ring,

G'

for hydrogen (a) or for the groups

stands in which

R ¹

for optionally substituted by halogen: C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₈ alkoxy-C ₂ -C ₈ alkyl, C ₁ -C ₈ alkylthio-C ₂ -C _8- alkyl, C ₁ -C ₈ -polyalkoxy-C ₂ -C ₈ -alkyl or cycloalkyl with 3-8 ring atoms, which can be interrupted by oxygen and / or sulfur atoms,
is optionally substituted by halogen, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ -haloalkoxy-substituted phenyl;
is optionally substituted by halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ -haloalkoxy-substituted phenyl-C ₁ -C ₆ alkyl stands,
represents pyridyl, pyrimidyl, thiazolyl and pyrazolyl optionally substituted by halogen and / or C ₁ -C ₆ alkyl,
represents phenoxy-C ₁ -C ₆ -alkyl optionally substituted by halogen and / or C ₁ -C ₆ -alkyl,

R ²

for optionally substituted by halogen: C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₈ alkoxy-C ₂ -C ₈ alkyl, C ₁ -C ₈ polyalkoxy-C ₂ -C ₈ alkyl,
is optionally substituted by halogen, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ -haloalkyl-substituted phenyl or benzyl,

R ³ , R ⁴ and R ⁵

independently of one another for C ₁ -C ₈ -alkyl optionally substituted by halogen, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -alkylamino, di- (C ₁ -C ₈ ) -alkylamino, C ₁ -C ₈ -alkylthio , C ₂ -C ₅ alkenylthio, C ₂ -C ₅ alkynylthio, C ₃ -C ₇ cycloalkylthio, for optionally by halogen, nitro, cyano, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl substituted phenyl, phenoxy or phenylthio,

R ⁶ and R ⁷

independently of one another for optionally substituted by halogen C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, C ₂ -C ₈ alkenyl, C ₁ -C ₂₀ alkoxy-C ₁ -C ₂₀ alkyl, for optionally by Halogen, C ₁ -C ₂₀ haloalkyl, C ₁ -C ₂₀ alkyl or C ₁ -C ₂₀ alkoxy substituted phenyl, for optionally halogen, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ haloalkyl or C ₁ -C ₂₀ alkoxy substituted benzyl or together represent a C ₂ -C ₆ alkylene ring which may be interrupted by oxygen,

and at least one agonist or antagonist of acetylcholine receptors of the formula (II) are synergistically active and are suitable for controlling animal pests. Because of this synergism, significantly smaller amounts of active ingredient can be used, ie the effect of the mixture is greater than the effect of the individual components.

X'

für C₁-C₄-Alkyl, Halogen, C₁-C₄-Alkoxy oder C₁-C₂-Halogenalkyl steht,

Y'

für Wasserstoff, C₁-C₄-Alkyl, Halogen, C₁-C₄-Alkoxy, C₁-C₂-Halogenalkyl steht,

Z'

für C₁-C₄-Alkyl, Halogen, C₁-C₄-Alkoxy steht,

n

für 0 oder 1 steht,

A' und B'

gemeinsam mit dem Kohlenstoffatom, an das sie gebunden sind einen gesättigten gegebenenfalls durch C₁-C₄-Alkyl, C₁-C₄-Alkoxy, substituierten 5- bis 6-gliedrigen Ring bilden,

G'

für Wasserstoff (a) oder für die Gruppen

in welchen

R¹

für gegebenenfalls durch Halogen substituiertes: C₁-C₁₆-Alkyl, C₂-C₁₆-Alkenyl, C₁-C₆-Alkoxy-C₂-C₆-alkyl, oder Cycloalkyl mit 3-7 Ringatomen, das durch 1 bis 2 Sauerstoff- und/oder Schwefelatome unterbrochen sein kann, steht,
für gegebenenfalls durch Halogen, Nitro, C₁-C₄-Alkyl, C₁-C₄-Alkoxy, C₁-C₃-Halogenalkyl, C₁-C₃-Halogenalkoxy-substituiertes Phenyl steht;

R²

für gegebenenfalls durch Halogen substituiertes: C₁-C₁₆-Alkyl, C₂-C₁₆-Alkenyl, C₁-C₆-Alkoxy-C₂-C₆-alkyl, steht,
für gegebenenfalls durch Halogen, Nitro, C₁-C₄-Alkyl, C₁-C₄-Alkoxy, C₁-C₄-Halogenalkyl-substituiertes Phenyl oder Benzyl steht,
und mindestens einen Agonisten bzw. Antagonisten von Acetylcholinrezeptoren der Formel (II).

Mixtures containing compounds of the formula (I) are preferred
in which

X '

represents C ₁ -C ₄ alkyl, halogen, C ₁ -C ₄ alkoxy or C ₁ -C ₂ haloalkyl,

Y '

represents hydrogen, C ₁ -C ₄ alkyl, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₂ haloalkyl,

Z '

represents C ₁ -C ₄ alkyl, halogen, C ₁ -C ₄ alkoxy,

n

represents 0 or 1,

A 'and B'

together with the carbon atom to which they are attached form a saturated 5- to 6-membered ring which is optionally substituted by C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy,

G'

for hydrogen (a) or for the groups

in which

R ¹

for optionally substituted by halogen: C ₁ -C ₁₆ alkyl, C ₂ -C ₁₆ alkenyl, C ₁ -C ₆ alkoxy-C ₂ -C ₆ alkyl, or cycloalkyl with 3-7 ring atoms, which is represented by 1 to 2 oxygen and / or sulfur atoms can be interrupted,
is optionally substituted by halogen, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkoxy is substituted phenyl;

R ²

represents optionally substituted by halogen: C ₁ -C ₁₆ alkyl, C ₂ -C ₁₆ alkenyl, C ₁ -C ₆ alkoxy-C ₂ -C ₆ alkyl,
-haloalkyl-substituted phenyl or benzyl is optionally substituted by halogen, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C _4,
and at least one agonist or antagonist of acetylcholine receptors of the formula (II).

und mindestens einen Agonisten bzw. Antagonisten von Acetylcholinrezeptoren der Formel (II).Mixtures containing the dihydrofuranone derivative of the formula (Ia) are particularly preferred

and at least one agonist or antagonist of acetylcholine receptors of the formula (II).

Europäische Offenlegungsschriften Nr. 464 830, 428 941, 425 978, 386 565, 383 091, 375 907, 364 844, 315 826, 259 738, 254 859, 235 725, 212 600, 192 060, 163 855, 154 178, 136 636, 136 686, 303 570, 302 833, 306 696, 189 972, 455 000, 135 956, 471 372, 302 389, 428 941, 376 279, 493 369, 580 553, 649 845, 685 477, 483 055, 580 553;

Deutsche Offenlegungsschriften Nr. 3 639 877, 3 712 307;

Japanische Offenlegungsschriften Nr. 03 220 176, 02 207 083, 63 307 857, 63 287 764, 03 246 283, 04 9371, 03 279 359, 03 255 072, 05 178 833, 07 173 157, 08 291 171;

US-Patentschriften Nr. 5 034 524, 4 948 798, 4 918 086, 5 039 686, 5 034 404, 5 532 365;

PCT-Anmeldungen Nr. WO 91/17 659, 91/4965;

Französische Anmeldung Nr. 2 611 114;

Brasilianische Anmeldung Nr. 88 03 621.

The agonists and antagonists of the nicotinergic acetylcholine receptors are known compounds which are known from the following publications:

European Patent Application Nos. 464 830, 428 941, 425 978, 386 565, 383 091, 375 907, 364 844, 315 826, 259 738, 254 859, 235 725, 212 600, 192 060, 163 855, 154 178, 136 636, 136 686, 303 570, 302 833, 306 696, 189 972, 455 000, 135 956, 471 372, 302 389, 428 941, 376 279, 493 369, 580 553, 649 845, 685 477, 483 055, 580 553;

German Offenlegungsschriften No. 3 639 877, 3 712 307;

Japanese Patent Laid-Open No. 03 220 176, 02 207 083, 63 307 857, 63 287 764, 03 246 283, 04 9371, 03 279 359, 03 255 072, 05 178 833, 07 173 157, 08 291 171;

U.S. Patent Nos. 5,034,524, 4,948,798, 4,918,086, 5,039,686, 5,034,404, 5,532,365;

PCT applications No. WO 91/17 659, 91/4965;

French Application No. 2 611 114;

Brazilian application No. 88 03 621.

The generic formulas and definitions described in these publications and the individual connections described therein are hereby expressly stated Referred.

These compounds are partly called nitromethylenes, nitroimines and related connections summarized.

in welcher

R

für Wasserstoff, gegebenenfalls substituierte Reste Acyl, Alkyl, Aryl, Aralkyl, Heterocyclyl, Heteroaryl oder Heteroarylalkyl steht;

A

für eine monofunktionelle Gruppe aus der Reihe Wasserstoff, Acyl, Alkyl, Aryl steht oder für eine bifunktionelle Gruppe steht, die mit dem Rest Z verknüpft ist;

E

für einen elektronenziehenden Rest steht;

X

für die Reste -CH= oder =N- steht, wobei der Rest -CH= anstelle eines H-Atoms mit dem Rest Z verknüpft sein kann;

Z

für eine monofunktionelle Gruppe aus der Reihe Alkyl, -O-R, -S-R,

steht,
wobei die Reste R gleich oder verschieden sind und die oben angegebene Bedeutung haben,
oder für eine bifunktionelle Gruppe steht, die mit dem Rest A oder dem Rest X verknüpft ist.

These compounds can preferably be summarized under the formula (II)

in which

R

represents hydrogen, optionally substituted radicals acyl, alkyl, aryl, aralkyl, heterocyclyl, heteroaryl or heteroarylalkyl;

A

represents a monofunctional group from the series hydrogen, acyl, alkyl, aryl or represents a bifunctional group which is linked to the radical Z;

e

represents an electron withdrawing group;

X

stands for the radicals -CH = or = N-, where the radical -CH = can be linked to the radical Z instead of an H atom;

Z

for a monofunctional group from the series alkyl, -OR, -SR,

stands,
where the radicals R are identical or different and have the meaning given above,
or represents a bifunctional group which is linked to the radical A or the radical X.

R

steht für Wasserstoff sowie für gegebenenfalls substituierte Reste aus der Reihe Acyl, Alkyl, Aryl, Aralkyl, Heterocyclylalkyl, Heteroaryl, Heteroarylalkyl.
Als Acylreste seien genannt Formyl, Alkylcarbonyl, Arylcarbonyl, Alkylsulfonyl, Arylsulfonyl, (Alkyl-)-(Aryl-)-phosphoryl, die ihrerseits substituiert sein können.
Als Alkyl sei genannt C₁-C₁₀-Alkyl, insbesondere C₁-C₄-Alkyl, im einzelnen Methyl, Ethyl, i-Propyl, sec.- oder t.-Butyl, die ihrerseits substituiert sein können.
Als Aryl sei genannt Phenyl, Naphthyl, insbesondere Phenyl.
Als Aralkyl sei genannt Phenylmethyl, Phenethyl.
Als Heterocyclylalkyl sei der Rest

genannt.
Als Heteroaryl sei genannt Heteroaryl mit bis zu 10 Ringatomen und N, O, S, insbesondere N als Heteroatomen. Im einzelnen seien genannt Thienyl, Furyl, Thiazolyl, Imidazolyl, Pyridyl, Benzthiazolyl, Pyridazinyl.
Als Heteroarylalkyl seien genannt Heteroarylmethyl, Heteroarylethyl mit bis zu 6 Ringatomen und N, O, S, insbesondere N als Heteroatomen, insbesondere gegebenenfalls substituiertes Heteroaryl wie unter Heteroaryl definiert.
Als Substituenten seien beispielhaft und vorzugsweise aufgeführt:

Alkyl mit vorzugsweise 1 bis 4, insbesondere 1 oder 2 Kohlenstoffatomen, wie Methyl, Ethyl, n- und i-Propyl und n-, i- und t-Butyl; Alkoxy mit vorzugsweise 1 bis 4, insbesondere 1 oder 2 Kohlenstoffatomen, wie Methoxy, Ethoxy, n- und i-Propyloxy und n-, i- und t-Butyloxy; Alkylthio mit vorzugsweise 1 bis 4, insbesondere 1 oder 2 Kohlenstoffatomen, wie Methylthio, Ethylthio, n- und i-Propylthio und n-, i- und t-Butylthio; Halogenalkyl mit vorzugsweise 1 bis 4, insbesondere 1 oder 2 Kohlenstoffatomen und vorzugsweise 1 bis 5, insbesondere 1 bis 3 Halogenatomen, wobei die Halogenatome gleich oder verschieden sind und als Halogenatome vorzugsweise Fluor, Chlor oder Brom, insbesondere Fluor stehen, wie Trifluormethyl, Hydroxy;

Halogen, vorzugsweise Fluor, Chlor, Brom und Iod, insbesondere Fluor, Chlor und Brom, Cyano; Nitro; Amino; Monoalkyl- und Dialkylamino mit vorzugsweise 1 bis 4, insbesondere 1 oder 2 Kohlenstoffatomen je Alkylgruppe, wie Methylamino, Methylethylamino, n- und i-Propylamino und Methyl-n-butylamino; Carboxyl; Carbalkoxy mit vorzugsweise 2 bis 4, insbesondere 2 oder 3 Kohlenstoffatomen, wie Carbomethoxy und Carboethoxy;

Sulfo (-SO₃H); Alkylsulfonyl mit vorzugsweise 1 bis 4, insbesondere 1 oder 2 Kohlenstoffatomen, wie Methylsulfonyl und Ethylsulfonyl; Arylsulfonyl mit vorzugsweise 6 oder 10 Arylkohlenstoffatomen, wie Phenylsulfonyl sowie Heteroarylamino und Heteroarylalkylamino wie Chlorpyridylamino und Chlorpyridylmethylamino.

A

steht für Wasserstoff oder für einen gegebenenfalls substituierten Rest aus der Reihe Acyl, Alkyl, Aryl, die bevorzugt die bei R angegebenen Bedeutungen haben, A steht ferner für eine bifunktionelle Gruppe. Genannt sei gegebenenfalls substituiertes Alkylen mit 1 bis 4, insbesondere 1 bis 2 C-Atomen, wobei als Substituenten die weiter oben aufgezählten Substituenten genannt seien (und wobei die Alkylengruppen durch Heteroatome aus der Reihe N, O, S unterbrochen sein können).

A und Z

können gemeinsam mit den Atomen, an welche sie gebunden sind, einen gesättigten oder ungesättigten heterocyclischen Ring bilden. Der heterocyclische Ring kann weitere 1 oder 2 gleiche oder verschiedene Heteroatome und/oder Heterogruppen enthalten. Als Heteroatome stehen vorzugsweise Sauerstoff, Schwefel oder Stickstoff und als Heterogruppen N-Alkyl, wobei Alkyl der N-Alkyl-Gruppe vorzugsweise 1 bis 4, insbesondere 1 oder 2 Kohlenstoffatome enthält. Als Alkyl seien Methyl, Ethyl, n- und i-Propyl und n-, i- und t-Butyl genannt. Der heterocyclische Ring enthält 5 bis 7, vorzugsweise 5 oder 6 Ringglieder.

Compounds of the formula (II) in which the radicals have the following meaning are particularly preferred:

R

represents hydrogen and optionally substituted radicals from the series acyl, alkyl, aryl, aralkyl, heterocyclylalkyl, heteroaryl, heteroarylalkyl.
Formyl, alkylcarbonyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, (alkyl-) - (aryl-) - phosphoryl, which in turn can be substituted, may be mentioned as acyl radicals.
C ₁ -C ₁₀ -Alkyl, in particular C ₁ -C ₄ -alkyl, in particular methyl, ethyl, i-propyl, sec.- or t.-butyl, which in turn may be substituted, may be mentioned as alkyl.
Phenyl, naphthyl, in particular phenyl, may be mentioned as aryl.
Phenylmethyl and phenethyl may be mentioned as aralkyl.
The rest is heterocyclylalkyl

called.
Heteroaryl with up to 10 ring atoms and N, O, S, in particular N as heteroatoms, may be mentioned as heteroaryl. In particular, thienyl, furyl, thiazolyl, imidazolyl, pyridyl, benzthiazolyl, pyridazinyl may be mentioned.
Heteroarylalkyl which may be mentioned are heteroarylmethyl, heteroarylethyl having up to 6 ring atoms and N, O, S, in particular N as heteroatoms, in particular optionally substituted heteroaryl as defined under heteroaryl.
Examples of preferred substituents are:

Alkyl having preferably 1 to 4, in particular 1 or 2 carbon atoms, such as methyl, ethyl, n- and i-propyl and n-, i- and t-butyl; Alkoxy preferably having 1 to 4, in particular 1 or 2, carbon atoms, such as methoxy, ethoxy, n- and i-propyloxy and n-, i- and t-butyloxy; Alkylthio with preferably 1 to 4, in particular 1 or 2 carbon atoms, such as methylthio, ethylthio, n- and i-propylthio and n-, i- and t-butylthio; Haloalkyl preferably having 1 to 4, in particular 1 or 2, carbon atoms and preferably 1 to 5, in particular 1 to 3, halogen atoms, the halogen atoms being the same or different and preferably being fluorine, chlorine or bromine, in particular fluorine, such as trifluoromethyl, hydroxy;

Halogen, preferably fluorine, chlorine, bromine and iodine, especially fluorine, chlorine and bromine, cyano; nitro; amino; Monoalkyl- and dialkylamino with preferably 1 to 4, in particular 1 or 2 carbon atoms per alkyl group, such as methylamino, methylethylamino, n- and i-propylamino and methyl-n-butylamino; carboxyl; Carbalkoxy preferably having 2 to 4, in particular 2 or 3, carbon atoms, such as carbomethoxy and carboethoxy;

Sulfo (-SO ₃ H); Alkylsulfonyl preferably having 1 to 4, in particular 1 or 2, carbon atoms, such as methylsulfonyl and ethylsulfonyl; Arylsulfonyl with preferably 6 or 10 aryl carbon atoms, such as phenylsulfonyl, and heteroarylamino and heteroarylalkylamino such as chloropyridylamino and chloropyridylmethylamino.

A

represents hydrogen or an optionally substituted radical from the series acyl, alkyl, aryl, which preferably have the meanings given for R, A furthermore represents a bifunctional group. Substituted alkylene with 1 to 4, in particular 1 to 2, carbon atoms may be mentioned, where the substituents listed above are mentioned as substituents (and the alkylene groups can be interrupted by heteroatoms from the series N, O, S).

A and Z

together with the atoms to which they are attached can form a saturated or unsaturated heterocyclic ring. The heterocyclic ring can contain a further 1 or 2 identical or different heteroatoms and / or hetero groups. The heteroatoms are preferably oxygen, sulfur or nitrogen and the hetero groups are N-alkyl, alkyl of the N-alkyl group preferably containing 1 to 4, in particular 1 or 2, carbon atoms. Alkyl, methyl, ethyl, n- and i-propyl and n-, i- and t-butyl may be mentioned. The heterocyclic ring contains 5 to 7, preferably 5 or 6 ring members.

in welchen

E, R und X

die oben und weiter unten genannten Bedeutungen haben.

E

steht für einen elektronenziehenden Rest, wobei insbesondere NO₂, CN, Halogenalkylcarbonyl wie Halogen-C₁-C₄-alkylcarbonyl, beispielsweise COCF₃, Alkylsulfonyl (z.B. SO₂-CH₃), Halogenalkylsulfonyl (z.B. SO₂CF₃) und ganz besonders NO₂ oder CN genannt seien.

X

steht für -CH= oder -N= .

Z

steht für einen gegebenenfalls substituierten Rest aus der Reihe Alkyl, -OR, -SR, -NRR, wobei R und die Substituenten bevorzugt die oben angegebene Bedeutung haben.

Z

kann außer dem obengenannten Ring gemeinsam mit dem Atom, an welches es gebunden ist und dem Rest

an der Stelle von X einen gesättigten oder ungesättigten heterocyclischen Ring bilden. Der heterocyclische Ring kann weitere 1 oder 2 gleiche oder verschiedene Heteroatome und/oder Heterogruppen enthalten. Als Heteroatome stehen vorzugsweise Sauerstoff, Schwefel oder Stickstoff und als Heterogruppen N-Alkyl, wobei die Alkyl oder N-Alkyl-Gruppe vorzugsweise 1 bis 4, vorzugsweise 1 oder 2 Kohlenstoffatome enthält. Als Alkyl seien Methyl, Ethyl, n- und i-Propyl und n-, i- und t-Butyl genannt. Der heterocyclische Ring enthält 5 bis 7, vorzugsweise 5 oder 6 Ringglieder. Als Beispiele für den heterocyclischen Ring seien Pyrrolidin, Piperidin, Piperazin, Hexamethylenimin, Morpholin und N-Methylpiperazin genannt.

Examples of the compounds of the formula (II) in which A and Z together with the atoms to which they are attached form a ring are the following:

in which

E, R and X

have the meanings given above and below.

e

stands for an electron-withdrawing radical, in particular NO ₂ , CN, haloalkylcarbonyl such as halogen-C ₁ -C ₄ -alkylcarbonyl, for example COCF ₃ , alkylsulfonyl (for example SO ₂ -CH ₃ ), haloalkylsulfonyl (for example SO ₂ CF ₃ ) and very particularly NO ₂ or CN may be mentioned.

X

stands for -CH = or -N =.

Z

stands for an optionally substituted radical from the series alkyl, -OR, -SR, -NRR, where R and the substituents preferably have the meaning given above.

Z

In addition to the ring mentioned above, it can be shared with the atom to which it is attached and the rest

form a saturated or unsaturated heterocyclic ring at the position of X. The heterocyclic ring can contain a further 1 or 2 identical or different heteroatoms and / or hetero groups. The heteroatoms are preferably oxygen, sulfur or nitrogen and the hetero groups are N-alkyl, the alkyl or N-alkyl group preferably containing 1 to 4, preferably 1 or 2, carbon atoms. Alkyl, methyl, ethyl, n- and i-propyl and n-, i- and t-butyl may be mentioned. The heterocyclic ring contains 5 to 7, preferably 5 or 6 ring members. Examples of the heterocyclic ring are pyrrolidine, piperidine, piperazine, hexamethyleneimine, morpholine and N-methylpiperazine.

R

für

steht, wobei

n

für 0, 1 oder 2, bevorzugt für 1 steht,

Subst.

für einen der oben aufgeführten Substituenten, besonders für Halogen, insbesondere für Chlor steht und A, Z, X und E die oben angegebene Bedeutung haben.

R

steht insbesondere für

oder

The agonists and antagonists of the nicotinergic acetylcholine receptors are particularly preferably compounds of the formula (II) in which

R

For

stands where

n

represents 0, 1 or 2, preferably 1,

N.

represents one of the substituents listed above, especially halogen, especially chlorine and A, Z, X and E have the meaning given above.

R

stands especially for

or

The following connections are specifically mentioned:

   insbesondere eine Verbindung der folgenden Formeln

oder

oder

oder

oder

Very particularly preferred agonists and antagonists of the nicotinergic acetylcholine receptors are compounds of the following formulas:

especially a combination of the following formulas

or

or

or

or

The compounds of the formulas (IIa), (IIk), (IIm) are very particularly preferred.

The compounds of the formulas (IIe), (IIg) are also very particularly preferred. (IIh), (IIl), (IIc).

A particularly preferred mixture contains the compound of formula (Ia) and the compound of formula (IIa);
a further particularly preferred mixture contains the compound of the formula (Ia) and the compound of the formula (IIk);
Mixtures containing the compound of the formula (Ia) and the compound of the formula (IIm) are further particularly preferred.

Aus der Ordnung der Isopoda z.B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

Aus der Ordnung der Diplopoda z.B. Blaniulus guttulatus.

Aus der Ordnung der Chilopoda z.B. Geophilus carpophagus, Scutigera spec.

Aus der Ordnung der Symphyla z.B. Scutigerella immaculata.

Aus der Ordnung der Thysanura z.B. Lepisma saccharina.

Aus der Ordnung der Collembola z.B. Onychiurus armatus.

Aus der Ordnung der Orthoptera z.B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

Aus der Ordnung der Dermaptera z.B. Forficula auricularia.

Aus der Ordnung der Isoptera z.B. Reticulitermes spp.

Aus der Ordnung der Anoplura z.B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

Aus der Ordnung der Mallophaga z.B. Trichodectes spp., Damalinea spp.

Aus der Ordnung der Thysanoptera z.B. Hercinothrips femoralis, Thrips tabaci.

Aus der Ordnung der Heteroptera z.B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

Aus der Ordnung der Homoptera z.B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Phylloxera vastatrix, Pemphigus spp., Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.

The active ingredient mixtures are suitable for plant pest tolerance and favorable warm-blood toxicity for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored products and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:

From the order of the Isopoda, for example Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example Lepisma saccharina.

From the order of the Collembola, for example Onychiurus armatus.

From the order of the Orthoptera, for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example Reticulitermes spp.

From the order of the anoplura, for example Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

From the order of the Mallophaga, for example Trichodectes spp., Damalinea spp.

From the order of the Thysanoptera, for example Hercinothrips femoralis, Thrips tabaci.

From the order of the Heteroptera, for example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera, for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Phusoponophumum, Phyododonoxum, Myzus sppera vastatrix, Pemphigus spp., Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.

From the order of the Lepidoptera, for example Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera sppi, Trichoplapsia s., Trichoplapsia n. , Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofinannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona viridima, Homona magnidana.
From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysoisusamasppas, Atomic spp. , Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermesles spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinusium sppyl., Ptinus holpp. Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
From the order of the Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca ., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
From the order of the Siphonaptera, for example Xenopsylla cheopis, Ceratophyllus spp.
From the order of the Arachnida, for example Scorpio maurus, Latrodectus mactans.
From the order of the Acarina, for example Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes, Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.

Plant-parasitic nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.

The ratio of the compounds of formula (I) used and the compounds of formula (II), as well as the total amount of the mixture depends on the type and occurrence dependent on the pests. The optimal conditions and total amounts used can be determined by test series for each application. in the general is the ratio of the compounds of formula (I) and the compounds of the formula (II) 1: 100 to 100: 1, preferably 1:25 to 25: 1 and especially preferably 1: 5 to 5: 1. These are parts by weight.

The active compound mixtures according to the invention can be in their commercially available formulations and in the use forms prepared from these formulations in a mixture with other active ingredients, such as insecticides, attractants, sterilants, Acaricides, nematicides, fungicides, growth regulators or herbicides available. Insecticides include, for example, phosphoric acid esters, carbamates, Carboxylic acid esters, chlorinated hydrocarbons, phenylureas, by Substances produced by microorganisms. In particular, the above are Insecticides and fungicides mentioned as mixing partners.

Phosphorsäureester wie Azinphos-ethyl, Azinphos-methyl, a-1(4-Chlorphenyl)-4-(O-ethyl, S-propyl)phosphoryloxy-pyrazol, Chlorpyrifos, Coumaphos, Demeton, Demeton-S-methyl, Diazinon, Dichlorvos, Dimethoate, Ethoate, Ethoprophos, Etrimfos, Fenitrothion, Fenthion, Heptenophas, Parathion, Parathion-methyl, Phosalone, Phoxim, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos, Prothiofos, Sulfprofos, Triazophos und Trichlorphon;

Carbamate wie Aldicarb, Bendiocarb, a-2-(1-Methylpropyl)-phenylmethylcarbamat, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Isoprocarb, Methomyl, Oxamyl, Pirimicarb, Promecarb, Propoxur und Thiodicarb;

Organosiliciumverbindungen, vorzugsweise Dimethyl(phenyl)silyl-methyl-3-phenoxybenzylether wie Dimethyl-(4-ethoxyphenyl)-silylmethyl-3-phenoxybenzylether oder

(Dimethylphenyl)-silyl-methyl-2-phenoxy-6-pyridylmethylether wie z.B. Dimethyl-(9-ethoxy-phenyl)-silylmethyl-2-phenoxy-6-pyridylmethylether oder [(Phenyl)-3-(3-phenoxyphenyl)-propyl](dimethyl)-silane wie z.B. (4-Ethoxyphenyl)-[3-(4-fluoro-3-phenoxyphenyl-propyl]dimethyl-silan, Silafluofen;

Pyrethroide wie Allethrin, Alphamethrin, Bioresmethrin, Byfenthrin, Cycloprothrin, Cyfluthrin, Decamethrin, Cyhalothrin, Cypermethrin, Deltamethrin, Alpha-cyano-3-phenyl-2-methylbenzyl-2,2-dimethyl-3-(2-chlor-2-trifluor-methylvinyl)cyclopropan-Carboxylat, Fenpropathrin, Fenfluthrin, Fenvalerate, Flucythrinate, Flumethrin, Fluvalinate, Permethrin, Resmethrin und Tralomethrin;

Nitroimine und Nitromethylene wie 1-[(6-Chlor-3-pyridinyl)-methyl]-4,5-dihydro-N-nitro-1H-imidazol-2-amin (Imidacloprid), N-[(6-Chlor-3-pyridyl)methyl-]N²-cyano-N¹-methylacetamide (NI-25);

Abamectin, AC 303.630, Acephate, Acrinathrin, Alanycarb, Aldoxycarb, Aldrin, Amitraz, Azamethiphos, Bacillus thuringiensis, Phosmet, Phosphamidon, Phosphine, Prallethrin, Propaphos, Propetamphos, Prothoate, Pyraclofos, Pyrethrins, Pyridaben, Pyridafenthion, Pyriproxyfen, Quinalphos, RH-7988, Rotenone, Sodium fluoride, Sodium hexafluorosilicate, Sulfotep, Sulfuryl fluoride, Tar Oils, Teflubenzuron, Tefluthrin, Temephos, Terbufos, Tetrachlorvinphos, Tetramethrin, O-2-tert.-Butylpyrimidin-5-yl-o-isopropyl-phosphorothiate, Thiocyclam, Thiofanox, Thiometon, Tralomethrin, Triflumuron, Trimethacarb, Vamidothion, Verticillium Lacanii, XMC, Xylylcarb, Benfuracarb, Bensultap, Bifenthrin, Bioallethrin, MERbioallethrin (S)-cyclopentenyl isomer, Bromophos, Bromophos-ethyl, Buprofezin, Cadusafos, Calcium Polysulfide, Carbophenothion, Cartap, Chinomethionat, Chlordane, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chloropicrin, Chlorpyrifos, Cyanophos, Beta-Cyfluthrin, Alpha-cypermethrin, Cyophenothrin, Cyromazine, Dazomet, DDT, Demeton-S-methylsulphon, Diafenthiuron, Dialifos, Dicrotophos, Diflubenzuron, Dinoseb, Deoxabenzofos, Diaxacarb, Disulfoton, DNOC, Empenthrin, Endosulfan, EPN, Esfenvalerate, Ethiofencarb, Ethion, Etofenprox, Fenobucarb, Fenoxycarb, Fensulfothion, Spinosynen, Flucycloxuron, Flufenprox, Flufenoxuron, Fonofos, Formetanate, Formothion, Fosmethilan, Furathiocarb, Heptachlor, Hexaflumuron, Hydramethylnon, Hydrogen Cyanide, Hydroprene, IPSP, Isazofos, Isofenphos, Isoprothiolane, Isoxathion, Iodfenphos, Kadethrin, Lindane, Malathion, Mecarbam, Mephosfolan, Mercurous, chloride, Metam, Metarthizium, anisopliae, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methoprene, Methoxychlor, Methyl isothiocyanate, Metholcarb, Mevinphos, Monocrotophos, Naled, Neodiprion sertifer NPV, Nicotine, Omethoate, Oxydemeton-methyl, Pentachlorophenol, Petroleum oils, Phenothrin, Phenthoate, Phorate.

Examples of insecticides that can be admixed are:

Phosphoric acid esters such as azinphos-ethyl, azinphos-methyl, a-1 (4-chlorophenyl) -4- (O-ethyl, S-propyl) phosphoryloxy-pyrazole, chlorpyrifos, Coumaphos, Demeton, Demeton-S-methyl, diazinon, dichlorvos, Dimethoate, Ethoate, Ethoprophos, Etrimfos, Fenitrothion, Fenthion, Heptenophas, Parathion, Parathion-methyl, Phosalone, Phoxim, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos, Prothiofos, Sulfprofos, Triazophos and Trichlorphon;

Carbamates such as aldicarb, bendiocarb, a-2- (1-methylpropyl) phenylmethyl carbamate, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, cloethocarb, isoprocarb, methomyl, oxamyl, pirimicarb, promecarb, propoxur and thiodicarb;

Organosilicon compounds, preferably dimethyl (phenyl) silylmethyl-3-phenoxybenzyl ether such as dimethyl (4-ethoxyphenyl) silylmethyl-3-phenoxybenzyl ether or

(Dimethylphenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether such as dimethyl- (9-ethoxyphenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether or [(phenyl) -3- (3-phenoxyphenyl) - propyl] (dimethyl) silanes such as (4-ethoxyphenyl) - [3- (4-fluoro-3-phenoxyphenyl-propyl] dimethyl silane, silafluofen;

Pyrethroids such as allethrin, alphamethrin, bioresmethrin, byfenthrin, cycloprothrin, cyfluthrin, decamethrin, cyhalothrin, cypermethrin, deltamethrin, alpha-cyano-3-phenyl-2-methylbenzyl-2,2-dimethyl-3- (2-chloro-2-trifluoromethyl) -methylvinyl) cyclopropane carboxylate, fenpropathrin, fenfluthrin, fenvalerate, flucythrinate, flumethrin, fluvalinate, permethrin, resmethrin and tralomethrin;

Nitroimines and nitromethylenes such as 1 - [(6-chloro-3-pyridinyl) methyl] -4,5-dihydro-N-nitro-1H-imidazol-2-amine (imidacloprid), N - [(6-chloro-3 -pyridyl) methyl-] N ² -cyano-N ¹ -methyl acetamide (NI-25);

Abamectin, AC 303.630, Acephate, Acrinathrin, Alanycarb, Aldoxycarb, Aldrin, Amitraz, Azamethiphos, Bacillus thuringiensis, Phosmet, Phosphamidon, Phosphine, Prallethrin, Propaphos, Propetamphos, Prothoate, Pyraclofos, Pyrethriproxyphid, Pyrethridafid, Pyrethrinsafid, Pyrethridafid, Pyrethrinsafid, Pyrethrinsphid, RH 7988, Rotenone, Sodium fluoride, Sodium hexafluorosilicate, Sulfotep, Sulfuryl fluoride, Tar Oils, Teflubenzuron, Tefluthrin, Temephos, Terbufos, Tetrachlorvinphos, Tetramethrin, O-2-tert.-Butylpyrimidin-5-yl-phosphoryl-o-isopropyl , Thiofanox, Thiometon, Tralomethrin, Triflumuron, Trimethacarb, Vamidothion, Verticillium Lacanii, XMC, Xylylcarb, Benfuracarb, Bensultap, Bifenthrin, Bioallethrin, MERbioallethrin (S) -cyclopentenyl, isomerophoside, Bromophenyl, Bromophenyl, Bromophenyl, isomer, Bromophenyl, isomer, Bromophenyl isomer, Bromophenyl, isomer, Bromophenyl, isomer, Bromophenyl, isomer, Bromophenyl, Bromophenyl isomer, Bromophenyl, Sulfur , Cartap, Chinomethionate, Chlordane, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chloropicrin, Chlorpyrifos, Cyanophos, Beta-Cyfluthrin, Alpha-cypermethrin, Cyophenothr in, Cyromazine, Dazomet, DDT, Demeton-S-methylsulphon, Diafenthiuron, Dialifos, Dicrotophos, Diflubenzuron, Dinoseb, Deoxabenzofos, Diaxacarb, Disulfoton, DNOC, Empenthrin, Endosulfan, EPN, Esfenvalxerate, Fenobarboxate, Feni Fensulfothion, Spinosynen, Flucycloxuron, Flufenprox, Flufenoxuron, Fonofos, Formetanate, Formothion, Fosmethilan, Furathiocarb, Heptachlor, Hexaflumuron, Hydramethylnon, Hydrogen Cyanide, Hydroprene, IPSP, Isazofos, Isofenphos, Isoxathionane, Isoprothionane , Mephosfolan, Mercurous, chloride, Metam, Metarthician, anisopliae, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methoprene, Methoxychlor, Methyl isothiocyanate, Metholcarb, Mevinphos, Monocrotophos, Naled, Neodiprion sertifer NPV, Nicotine Oxomol, Oxotol, Oxotol, Oxotol, Oxotol, Oxotol, Oxotol, Oxotol, Oxotol, Oxotol, Oxotol, Methotol Petroleum oils, phenothrin, phenthoates, phorates.

The additional insecticides which may also be admixed can also be used the class of compounds of the general formula (I).

Triazole wie:

Azaconazole, Propiconazole, Tebuconazole, Cyproconazole, Metconazole, Amitrole, Azocyclotin, BAS 480F, Bitertanol, Difenoconazole, Fenbuconazole, Fenchlorazole, Fenethanil, Fluquinconazole, Flusilazole, Flutriafol, Imibenconazole, Isozofos, Myclobutanil, Paclobutrazol, (±)-cis-1-(4-chlorphenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol, Tetraconazole, Triadimefon, Triadimenol, Triapenthenol, Triflumizole, Triticonazole, Uniconazole sowie deren Metallsalze und Säureaddukte.

Imidazole wie:

Imazalil, Pefurazoate, Prochloraz, Triflumizole, 2-(1-tert-Butyl)-1-(2-chlorphenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol, Thiazolcarboxanilide wie 2',6'-Dibromo-2-methyl-4-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide, 1-Imidazolyl-1-(4'chlorophenoxy)-3,3-dimethylbutan-2-on sowie deren Metallsalze und Säureaddukte.

Methyl(E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]3-methoxyacrylate, methyl(E)-2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[6-(2-fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[6-(2,6-difluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(5-methylpyrimidin-2-yloxy)-phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(phenyl-sulfonyloxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(4-nitrophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-phenoxyphenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dimethylbenzoyl)pyrrol-1-yl]-3-methoxyacrylate, methyl(E)-2-[2-(3-methoxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(2-pheny]ethen-1-yl)-phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dichlorophenoxy)pyridin-3-yl]-3-methoxyacrylate, methyl(E)-2-(2-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)phenyl)-3-methoxyacrylate, methyl(E)-2-(2-[3-(alpha-hydroxybenzyl)phenoxy]phenyl)-3-methoxyacrylate, methyl(E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl)-3-methoxyacrylate, methyl(E)-2-[2-(3-n-propyloxyphenoxy)phenyl]3-methoxyacrylate, methyl(E)-2-[2-(3-isopropyloxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(2-fluorophenoxy)pehnoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3-ethoxyphenoxy)-phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(4-tert.-butylpyridin-2-yloxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3-methylpyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[6-(2-methylphenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(5-bromopyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate, methyl(E)-2-(2-(3-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, (E),(E)methyl-2-[2-(5,6-dimethylpyrazin-2-ylmethyloximinomethyl)phenyl]-3-methoxyacrylate, (E)-methyl-2-{2-[6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate, (E),(E)methyl-2-{2-(3-methoxyphenyl)methyloximinomethyl]phenyl}-3-methoxyacrylate, (E)methyl-2-{2-(6-(2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}3-methoxyacrylate, (E),(E)methyl-2-{2-[6-phenylpyrimidin-4-yl)-methyloximinomethyl]phenyl}-3-methoxyacrylate, (E),(E)methyl-2-{2-[(4-chlorophenyl)-methyloximinomethyl]phenyl}-3-methoxyacrylate, (E)methyl-2-{2-[6-(2-n-propylphenoxy)-1,3,5-triazin-4-yloxy]phenyl}-3-methoxyacrylate, (E),(E)-methyl-2- {2-[(3-nitrophenyl)methyloximinomethyl]phenyl }-3-methoxyacrylate;

Succinat-Dehydrogenase Inhibitoren wie:

Fenfuram, Furcarbanil, Cyclafluramid, Furmecyclox, Seedvax, Metsulfovax, Pyrocarbolid, Oxycarboxin, Shirlan, Mebenil (Mepronil), Benodanil, Flutolanil (Moncut);

Naphthalin-Derivate wie Terbinafine, Naftifine, Butenafine, 3-Chloro-7-(2-aza-2,7,7-trimethyl-oct-3-en-5-in);

Sulfenamide wie Dichlofluanid, Tolylfluanid, Folpet, Fluorfolpet; Captan, Captofol;

Benzimidazole wie Carbendazim, Benomyl, Furathiocarb, Fuberidazole, Thiophonatmethyl, Thiabendazole oder deren Salze;

Morpholinderivate wie Fenpropimorph, Falimorph, Dimethomorph, Dodemorph, Aldimorph, Fenpropidin und ihre arylsulfonsauren Salze, wie z.B. p-Toluolsulfonsäure und p-Dodecylphenyl-sulfonsäure;

Dithiocarbamate, Cufraneb, Ferbam, Mancopper, Mancozeb, Maneb, Metam, Metiram, Thiram Zeneb, Ziram;

Benzthiazole wie 2-Mercaptobenzothiazol;

Benzamide wie 2,6-Dichloro-N-(4-trifluoromethylbenzyl)-benzamide;

Borverbindungen wie Borsäure, Borsäureester, Borax;

Formaldehyd und Formaldehydabspaltende Verbindungen wie Benzylalkoholmono-(poly)-hemiformal, Oxazolidine, Hexa-hydro-S-triazine, N-Methylolchloracetamid, Paraformadehyd, Nitropyrin, Oxolinsäure, Tecloftalam;

Tris-N-(cyclohexyldiazeniumdioxy)-aluminium, N-(Cyclo-hexyldiazeniumdioxy)-tributylzinn bzw. K-Salze, Bis-N-(cyclohexyldiazeniumdioxy)-kupfer;

N-Methylisothiazolin-3-on, 5-Chlor-N-methylisothiazolin-3-on, 4,5-Dichloro-N-octylisothiazolin-3-on, N-Octyl-isothiazolin-3-on, 4,5-Trimethylen-isothiazolinone, 4,5-Benzisothiazolinone, N-Methylolchloracetamid;

Aldehyde wie Zimtaldehyd, Formaldehyd, Glutardialdehyd, β-Bromzimtaldehyd; Thiocyanate wie Thiocyanatomethylthiobenzothiazol, Methylenbisthiocyanat, usw;

quartäre Ammoniumverbindungen wie Benzyldimethyltetradecylammoniumchlorid, Benzyldimethyldodecylammoniumchlorid, Didecyldimethaylammoniumchlorid;

Iodderivate wie Diiodmethyl-p-tolylsulfon, 3-Iod-2-propinyl-alkohol, 4-Chlorphenyl-3-iodpropargylformal, 3-Brom-2,3-diiod-2-propenylethylcarbamat, 2,3,3-Triiodallylalkohol, 3-Brom-2,3-diiod-2-propenylalkohol, 3-Iod-2-propinyl-n-butylcarbamat, 3-Iod-2-propinyl-n-hexylcarbamat, 3-Iod-2-propinyl-cyclohexylcarbamat, 3-Iod-2-propinyl-phenylcarbamat;

Phenolderivate wie Tribromphenol, Tetrachlorphenol, 3-Methyl-4-chlorphenol, 3,5-Dimethyl-4-chlorphenol, Phenoxyethanol, Dichlorphen, o-Phenylphenol, m-Phenylphenol, p-Phenylphenol, 2-Benzyl-4-chlorphenol und deren Alkali- und Erdalkalimetallsalze;

Mikrobizide mit aktivierter Halogengruppe wie Chloracetamid, Bronopol, Bronidox, Tectamer wie 2-Brom-2-nitro-1,3-propandiol, 2-Brom-4'-hydroxy-acetophenon, 2,2-Dibrom-3-nitril-propionamid, 1,2-Dibrom-2,4-dicyanobutan, β-Brom-β-nitrostyrol;

Pyridine wie 1-Hydroxy-2-pyridinthion (und ihre Na-, Fe-, Mn-, Zn-Salze), Tetrachlor-4-methylsulfonylpyridin, Pyrimethanol, Mepanipyrim, Dipyrithion, 1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridin;

Metallseifen wie Zinn-, Kupfer-, Zinknaphtenat, -octoat, 2-ethylhexanoat, -oleat, -phosphat, -benzoat;

Metallsalze wie Kupferhydroxycarbonat, Natriumdichromat, Kaliumdichromat, Kaliumchromat, Kupfersulfat, Kupferchlorid, Kupferborat, Zinkfluorosilikat, Kupferfluorosilikat, insbesondere Mischung mit Fixiermitteln;

Oxide wie Tributylzinnoxid, Cu₂O, CuO, ZnO;

Dialkyldithiocarbamate wie Na- und Zn-Salze von Dialkyldithiocarbamaten, Tetramethylthiuramdisulfid, Kalium-N-methyl-dithiocarbamat;

Nitrile wie 2,4,5,6-Tetrachlorisophthalodinitril, Dinatrium-cyano-dithioimidocarbamat;

Chinoline wie 8-Hydroxychinolin und deren Cu-Salze;

Mucochlorsäure, 5-Hydroxy-2(5H)-furanon;

4,5-Dichlorodithiazolinon, 4,5-Benzdithiazolinon, 4,5-Trimethylendithiazolinon, 4,5-Dichlor-(3H)-1,2-dithiol-3-on, 3,5-Dimethyl-tetrahydro-1,3,5-thiadiazin-2-thion,

N-(2-p-Chlorbenzoylethyl)-hexaminiumchlorid, Kalium-N-hydroxymethyl-N'-methyl-dithiocarbamat,

2-Oxo-2-(4-hydroxy-phenyl)acethydroximsäure-chlorid,

Phenyl-(2-chlor-cyan-vinyl)sulfon,

Phenyl-(1,2-dichlor-2-cyan-vinyl)sulfon;

Ag, Zn oder Cu-haltige Zeolithe allein oder eingeschlossen in polymere Wirkstoffe, oder auch Mischungen aus mehrern der oben genannten Fungizide.

Possible fungicides which can still be admixed are preferably:

Triazoles such as:

Azaconazole, Propiconazole, Tebuconazole, Cyproconazole, Metconazole, Amitrole, Azocyclotin, BAS 480F, Bitertanol, Difenoconazole, Fenbuconazole, Fenchlorazole, Fenethanil, Fluquinconazole, Flusilazole, Flutriafol, Imibenconazol, 1- isobonosoloblazolobrazole (1-5) 4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -cycloheptanol, tetraconazole, triadimefon, triadimenol, triapenthenol, triflumizole, triticonazole, uniconazole and their metal salts and acid adducts.

Imidazoles such as:

Imazalil, pefurazoate, prochloraz, triflumizole, 2- (1-tert-butyl) -1- (2-chlorophenyl) -3- (1,2,4-triazol-1-yl) propan-2-ol, thiazolecarboxanilides such as 2 ', 6'-Dibromo-2-methyl-4-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide, 1-imidazolyl-1- (4'chlorophenoxy) -3,3-dimethylbutane-2 -on and their metal salts and acid adducts.

Methyl ( E ) -2- [2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl] 3-methoxyacrylates, methyl ( E ) -2- [2- [6- (2-thioamidophenoxy) pyrimidine- 4-yloxy] phenyl] -3-methoxyacrylate, methyl ( E ) -2- [2- [6- (2-fluorophenoxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, methyl ( E ) -2- [ 2- [6- (2,6-difluorophenoxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylates, methyl ( E ) -2- [2- [3- (pyrimidin-2-yloxy) phenoxy] phenyl] - 3-methoxyacrylate, methyl ( E ) -2- [2- [3- (5-methylpyrimidin-2-yloxy) phenoxy] phenyl] -3-methoxyacrylate, methyl ( E ) -2- [2- [3- ( phenyl-sulfonyloxy) phenoxy] phenyl] -3-methoxyacrylate, methyl ( E ) -2- [2- [3- (4-nitrophenoxy) phenoxy] phenyl] -3-methoxyacrylate, methyl ( E ) -2- [2- phenoxyphenyl] -3-methoxyacrylate, methyl ( E ) -2- [2- (3,5-dimethylbenzoyl) pyrrol-1-yl] -3-methoxyacrylate, methyl ( E ) -2- [2- (3-methoxyphenoxy) phenyl] -3-methoxyacrylate, methyl ( E ) -2- [2- (2-pheny] ethen-1-yl) phenyl] -3-methoxyacrylate, methyl ( E ) -2- [2- (3.5 -dichlorophenoxy) pyridin-3-yl] -3-methoxyacrylate, methyl ( E ) -2- (2- (3- (1,1,2,2-tetrafluoroethox y) phenoxy) phenyl) -3-methoxyacrylate, methyl ( E ) -2- (2- [3- (alpha-hydroxybenzyl) phenoxy] phenyl) -3-methoxyacrylate, methyl ( E ) -2- (2- (4th -phenoxypyridin-2-yloxy) phenyl) -3-methoxyacrylate, methyl ( E ) -2- [2- (3-n-propyloxyphenoxy) phenyl] 3-methoxyacrylate, methyl ( E ) -2- [2- (3- isopropyloxyphenoxy) phenyl] -3-methoxyacrylate, methyl ( E ) -2- [2- [3- (2-fluorophenoxy) phenoxy] phenyl] -3-methoxyacrylate, methyl ( E ) -2- [2- (3-ethoxyphenoxy ) -phenyl] -3-methoxyacrylate, methyl ( E ) -2- [2- (4-tert-butylpyridin-2-yloxy) phenyl] -3-methoxyacrylate, methyl ( E ) -2- [2- [3rd - (3-cyanophenoxy) phenoxy] phenyl] -3-methoxyacrylate, methyl ( E ) -2- [2- (3-methylpyridin-2-yloxymethyl) phenyl] -3-methoxyacrylate, methyl ( E ) -2- [2 - [6- (2-methylphenoxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, methyl ( E ) -2- [2- (5-bromopyridin-2-yloxymethyl) phenyl] -3-methoxyacrylate, methyl ( E ) -2- (2- (3- (3-iodopyridin-2-yloxy) phenoxy) phenyl] -3-methoxyacrylate, methyl ( E ) -2- [2- [6- (2-chloropyridin-3-yloxy ) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, ( E ), ( E ) methyl-2- [2- (5,6-dimethylpyrazin-2-ylmethyloximinomethyl) phenyl] -3-methoxyacrylate, (E) -methyl-2- {2- [6- (6-methylpyridin-2-yloxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate, ( E ), ( E ) methyl-2- {2- (3-methoxyphenyl) methyloximinomethyl] phenyl} -3-methoxyacrylate, ( E ) methyl-2- {2 - (6- (2-azidophenoxy) pyrimidin-4-yloxy] phenyl} 3-methoxyacrylates, ( E ), ( E ) methyl-2- {2- [6-phenylpyrimidin-4-yl) methyloximinomethyl] phenyl} -3-methoxyacrylate, ( E ), ( E ) methyl-2- {2 - [(4-chlorophenyl) methyloximinomethyl] phenyl} -3-methoxyacrylate, ( E ) methyl-2- {2- [6- (2nd -n-propylphenoxy) -1,3,5-triazin-4-yloxy] phenyl} -3-methoxyacrylate, ( E ), ( E ) -methyl-2- {2 - [(3-nitrophenyl) methyloximinomethyl] phenyl} -3-methoxyacrylate;

Succinate dehydrogenase inhibitors such as:

Fenfuram, furcarbanil, cyclafluramide, furmecyclox, seedvax, metsulfovax, pyrocarbolide, oxycarboxin, shirlan, mebenil (mepronil), benodanil, flutolanil (moncut);

Naphthalene derivatives such as terbinafine, naftifine, butenafine, 3-chloro-7- (2-aza-2,7,7-trimethyl-oct-3-en-5-in);

Sulfenamides such as dichlofluanid, tolylfluanid, folpet, fluorfolpet; Captan, Captofol;

Benzimidazoles such as carbendazim, benomyl, furathiocarb, fuberidazole, thiophonate methyl, thiabendazole or their salts;

Morpholine derivatives such as fenpropimorph, falimorph, dimethomorph, dodemorph, aldimorph, fenpropidine and their arylsulfonic acid salts, such as, for example, p-toluenesulfonic acid and p-dodecylphenylsulfonic acid;

Dithiocarbamate, Cufraneb, Ferbam, Mancopper, Mancozeb, Maneb, Metam, Metiram, Thiram Zeneb, Ziram;

Benzothiazoles such as 2-mercaptobenzothiazole;

Benzamides such as 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide;

Boron compounds such as boric acid, boric acid ester, borax;

Formaldehyde and formaldehyde releasing compounds such as benzyl alcohol mono- (poly) hemiformal, oxazolidines, hexa-hydro-S-triazines, N-methylolchloroacetamide, paraformadehyde, nitropyrin, oxolinic acid, tecloftalam;

Tris-N- (cyclohexyldiazeniumdioxy) aluminum, N- (cyclohexyldiazeniumdioxy) -tributyltin or K salts, bis-N- (cyclohexyldiazeniumdioxy) copper;

N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4,5-dichloro-N-octylisothiazolin-3-one, N-octyl-isothiazolin-3-one, 4,5-trimethylene isothiazolinone, 4,5-benzisothiazolinone, N-methylolchloroacetamide;

Aldehydes such as cinnamaldehyde, formaldehyde, glutardialdehyde, β-bromocinnamaldehyde; Thiocyanates such as thiocyanatomethylthiobenzothiazole, methylene bisthiocyanate, etc;

quaternary ammonium compounds such as benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, didecyldimethaylammonium chloride;

Iodine derivatives such as diiodomethyl p-tolyl sulfone, 3-iodo-2-propynyl alcohol, 4-chlorophenyl-3-iodopropargyl formal, 3-bromo-2,3-diiodo-2-propenylethyl carbamate, 2,3,3-triiodallyl alcohol, 3- Bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propynyl-n-butyl carbamate, 3-iodo-2-propynyl-n-hexyl carbamate, 3-iodo-2-propynyl-cyclohexyl carbamate, 3-iodo 2-propynyl-phenylcarbamate;

Phenol derivatives such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophen, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol and their alkali - and alkaline earth metal salts;

Microbicides with activated halogen group such as chloroacetamide, bronopol, bronidox, tectamer such as 2-bromo-2-nitro-1,3-propanediol, 2-bromo-4'-hydroxy-acetophenone, 2,2-dibromo-3-nitrile-propionamide, 1,2-dibromo-2,4-dicyanobutane, β-bromo-β-nitrostyrene;

Pyridines such as 1-hydroxy-2-pyridinthione (and their Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine, pyrimethanol, mepanipyrim, dipyrithione, 1-hydroxy-4-methyl-6- (2nd , 4,4-trimethylpentyl) -2 (1H) -pyridine;

Metal soaps such as tin, copper, zinc naphtenate, octoate, 2-ethylhexanoate, oleate, phosphate, benzoate;

Metal salts such as copper hydroxycarbonate, sodium dichromate, potassium dichromate, potassium chromate, copper sulfate, copper chloride, copper borate, zinc fluorosilicate, copper fluorosilicate, in particular a mixture with fixing agents;

Oxides such as tributyltin oxide, Cu ₂ O, CuO, ZnO;

Dialkyldithiocarbamates such as Na and Zn salts of dialkyldithiocarbamates, tetramethylthiuram disulfide, potassium N-methyldithiocarbamate;

Nitriles such as 2,4,5,6-tetrachloroisophthalonitrile, disodium cyano-dithioimidocarbamate;

Quinolines such as 8-hydroxyquinoline and their Cu salts;

Mucochloric acid, 5-hydroxy-2 (5H) furanone;

4,5-dichlorodithiazolinone, 4,5-benzdithiazolinone, 4,5-trimethylene-dithiazolinone, 4,5-dichloro- (3H) -1,2-dithiol-3-one, 3,5-dimethyl-tetrahydro-1,3, 5-thiadiazine-2-thione,

N- (2-p-chlorobenzoylethyl) hexaminium chloride, potassium N-hydroxymethyl-N'-methyldithiocarbamate,

2-Oxo-2- (4-hydroxy-phenyl) acethydroximsäure chloride,

Phenyl (2-chloro-cyano-vinyl) sulfone,

Phenyl- (1,2-dichloro-2-cyano-vinyl) sulfone;

Zeolites containing Ag, Zn or Cu alone or included in polymeric active ingredients, or else mixtures of several of the above-mentioned fungicides.

The active substance content of the use forms prepared from the commercially available formulations can vary widely. The drug concentration of the Use forms can be from 0.0000001 to 95% by weight of active compound, preferably are between 0.0001 and 1% by weight.

The active ingredient mixtures can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, Aerosols, active ingredient-impregnated natural and synthetic substances, fine encapsulation in polymeric substances and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals, etc., as well as ULV cold and Warm mist formulations.

These formulations are made in a known manner, e.g. by mixing of the active substances with extenders, i.e. liquid solvents, under pressure liquefied gases and / or solid carriers, optionally using of surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-generating agents. In case of using water as Extenders can e.g. organic solvents are also used as auxiliary solvents become. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, Alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar Solvents such as dimethylformamide and dimethyl sulfoxide, and water; With Liquefied gaseous extenders or carriers are such liquids meant which are gaseous at normal temperature and pressure, e.g. Aerosol propellant, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; solid carriers are possible: e.g. natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, Alumina and silicates; come as solid carriers for granules in question: e.g. broken and fractionated natural rocks such as calcite, marble, Pumice, sepiolite, dolomite and synthetic granules from inorganic and organic Flours and granules from organic material such as sawdust, coconut shells, Corn cobs and tobacco stalks; as an emulsifier and / or foam generator Funds are possible: e.g. non-ionic and anionic emulsifiers, such as Polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl ether, Alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.

Adhesives such as carboxymethylcellulose, natural, can be used in the formulations and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids such as cephalins and lecithins, and synthetic phospholipids. Further Additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient mixture, preferably between 0.5 and 90 percent by weight of active ingredient mixture.

The mixtures according to the invention can be applied over the sheet.

According to the invention, all plants and parts of plants can be treated. Under Plants are understood here as all plants and plant populations desired and undesirable wild plants or crops (including naturally occurring crops). Cultivated plants can be plants that by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these Methods can be obtained, including transgenic plants and including those that can or cannot be protected by plant variety rights Plant varieties. Under plant parts, all above-ground and underground Parts and organs of plants, such as shoot, leaf, flower and root understood leaves, needles, stems, stems, flowers, fruiting bodies, Fruits and seeds as well as roots, tubers and rhizomes are listed. To the Plant parts also include crops as well as vegetative and generative Propagation material, for example cuttings, tubers, rhizomes, offshoots and Seeds.

The treatment of the plants and plant parts according to the invention with the Active substances take place directly or by influencing their environment, living space or storage room according to the usual treatment methods, e.g. by diving, Spraying, vaporizing, atomizing, scattering, spreading and in the case of propagation material, especially in the case of seeds, further by single or multi-layer coating.

When using the active compound combinations according to the invention, the application rates can can be varied within a wide range depending on the type of application. When treating parts of plants, the amounts of active ingredient combination are applied generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.

The good insecticidal and acaricidal activity of the active compound combinations according to the invention can be seen from the following examples. While the individual Combinations show weaknesses in their effectiveness Effect that goes beyond a simple summation of effects.

Insecticides and acaricides always have a synergistic effect if the effect of the active ingredient combinations is greater than the sum of the effects of the individually applied active ingredients.

X

den Wirkungsgrad beim Einsatz des Wirkstoffes A in einer Aufwandmenge von m g/ha oder in einer Konzentration von m ppm bedeutet,

Y

den Wirkungsgrad beim Einsatz des Wirkstoffes B in einer Aufwandmenge von n g/ha oder in einer Konzentration von n ppm bedeutet und

E

den Wirkungsgrad beim Einsatz der Wirkstoffe A und B in Aufwandmengen von m und n g/ha oder in einer Konzentration von m und n ppm bedeutet,

dann ist E=X + Y - X·Y100 The expected effect for a given combination of two active ingredients can be calculated according to SR Colby, Weeds 15 (1967), 20-22) as follows:
If

X

means the efficiency when using the active ingredient A in an application rate of m g / ha or in a concentration of m ppm,

Y

means the efficiency when using the active ingredient B in an application rate of n g / ha or in a concentration of n ppm and

e

means the efficiency when using active ingredients A and B in application rates of m and n g / ha or in a concentration of m and n ppm,

then E = X + Y - X * Y 100

The efficiency is determined in%. It means 0% efficiency corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.

If the actual effect is greater than calculated, the combination is in its Effect over additive, i.e. there is a synergistic effect. In this case the actual observed efficiency may be greater than that from the above Formula calculated value for the expected efficiency (E).

Example A

Aphis gossypii test solvent 3 parts by weight of dimethylformamide emulsifier 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight is mixed Active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

Cotton leaves (Gossypium hirsutum) that are heavily affected by the cotton aphid (Aphis gossypii) are infested, are immersed in the preparation of the active ingredient of the desired Concentration treated.

After the desired time, the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids are killed were. The determined kill rates are calculated using the Colby formula.

In this test, for example, the following combination of active ingredients according to the present application shows a synergistically enhanced effectiveness compared to the individually used active ingredients: page 1
plant-damaging insect Aphis gossypii test drugs Active substance concentration in ppm Degree of killing in% after 6 ^d Ex. (Ia) known 1.6 0 Ex. (IIa) known 1.6 85 Ex. (Ia) + Ex. (IIa) according to the invention 1.6 + 1.6 found * / 95 calc. ** / 85 found * = found effect calc. ** = Effect calculated according to the Colby formula page 2
plant-damaging insects
Aphis gossypii test drugs Active substance concentration in ppm Degree of killing in% after 6 ^d Ex. (Ia) known 1.6 0 Ex. (IIk) known 1.6 55 Ex. (Ia) + Ex. (IIk) according to the invention 1.6 + 1.6 found * / 95 calc. ** / 55 found * = found effect calc. ** = Effect calculated according to the Colby formula

Example B

Aphis gossypii test / larval mortality Solvent: 3 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight is mixed Active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

Cotton leaves (Gossypium hirsutum) that are heavily infested with adults and larvae Cotton aphids (Aphis gossypii) are infested by diving into the Active ingredient preparation of the desired concentration treated.

After the desired time, the larvae are killed in%. there means 100% that all larvae have been killed; 0% means that there are no larvae were killed. The determined kill rates are calculated using the Colby formula.

In this test, for example, the following combination of active ingredients according to the present application shows a synergistically enhanced effectiveness compared to the individually used active ingredients: page 1
plant-damaging insects
Aphis gossypii test / larval mortality drugs Active substance concentration in ppm Degree of killing in% after 6 ^d Ex. (Ia) known 1.6 0 Ex. (IIa) known 1.6 80 Ex. (Ia) + Ex. (IIa) according to the invention 1.6 + 1.6 found * / 95 calc. ** / 80 found * = found effect calc. ** = Effect calculated according to the Colby formula page 2
plant-damaging insects
Aphis gossypii test / larval mortality drugs Active substance concentration in ppm Degree of killing in% after 6 ^d Ex. (Ia) known 1.6 0 Ex. (IIk) known 1.6 60 Ex. (Ia) + Ex. (IIk) according to the invention 1.6 + 1.6 found * / 95 calc. ** / 60 found * = found effect calc. ** = Effect calculated according to the Colby formula

Example C

Myzus Test solvent 3 parts by weight of dimethylformamide emulsifier 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight is mixed Active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

Cabbage leaves (Brassica oleracea) heavily from the peach aphid (Myzus persicae) are infested, are dipped into the active ingredient preparation of the desired Concentration treated.

After the desired time, the kill is determined in%. 100% means that all animals were killed; 0% means that no animals have been killed. The determined kill rates are calculated using the Colby formula.

In this test, for example, the following combination of active ingredients according to the present application shows a synergistically enhanced effectiveness compared to the individually used active ingredients: plant-damaging insects
Myzus Test drugs Active substance concentration in ppm Kill rate in% after 1 ^d Ex. (Ia) known 1.6 0 Ex. (IIa) known 1.6 70 Ex. (Ia) + Ex. (IIa) according to the invention 1.6 + 1.6 found * / 98 calc. ** / 70 found * = found effect calc. ** = Effect calculated according to the Colby formula

Example D

Myzus Test / Larvalmortalität solvent 3 parts by weight of dimethylformamide emulsifier 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight is mixed Active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

Cabbage leaves (Brassica oleracea), heavily of peach aphid adults and larvae (Myzus persicae) are infested by diving into the active ingredient preparation of the desired concentration

After the desired time, the larvae are killed in%. there means 100% that all larvae have been killed; 0% means that there are no larvae were killed. The determined kill rates are calculated using the Colby formula.

In this test, for example, the following combination of active ingredients according to the present application shows a synergistically enhanced effectiveness compared to the individually used active ingredients: plant-damaging insects
Myzus Test / Larvalmortalität drugs Active substance concentration in ppm Degree of killing in% after 6 ^d Ex. (Ia) known 0.32 0 Ex. (IIa) known 0.32 0 Ex. (Ia) + Ex. (IIa) according to the invention 0.32 + 0.32 found * / 55 calc. ** / 0 found * = found effect calc. ** = Effect calculated according to the Colby formula

Claims (8)

1. Composition, comprising a synergistically effective mixture of compounds of the formula (I)

   

   in which

   X'

   represents C₁-C₆-alkyl, halogen, C₁-C₆-alkoxy or C₁-C₃-halogenoalkyl,

   Y'

   represents hydrogen, C₁-C₆-alkyl, halogen, C₁-C₆-alkoxy, C₁-C₃-halogenoalkyl,

   Z'

   represents C₁-C₆-alkyl, halogen, C₁-C₆-alkoxy,

   n

   represents a number from 0 to 3,

   A' and B'

   are identical or different and each represents hydrogen or in each case optionally halogen-substituted straight-chain or branched C₁-C₁₂-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkinyl, C₁-C₁₀-alkoxy-C₂-C₈-alkyl, C₁-C₈-polyalkoxy-C₂-C₈-alkyl, C₁-C₁₀-alkylthio-C₂-C₈-alkyl, cycloalkyl having 3-8 ring atoms which may be interrupted by oxygen and/or sulphur and in each case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkoxy- and/or nitro-substituted phenyl or phenyl-C₁-C₆-alkyl,

   or in which

   A' and B'

   together with the carbon atom to which they are attached form a saturated or unsaturated 3- to 8-membered ring which is optionally interrupted by oxygen and/or sulphur and is optionally substituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, C₁-C₄-alkylthio or optionally substituted phenyl or is optionally benzo-fused,

   G'

   represents hydrogen (a) or represents the groups

   

   

   in which

   R¹

   represents in each case optionally halogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl, C₁-C₈-alkylthio-C₂-C₈-alkyl, C₁-C₈-polyalkoxy-C₂-C₈-alkyl or cycloalkyl having 3-8 ring members which may be interrupted by oxygen and/or sulphur atoms,
   represents optionally halogen-, nitro-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl-and/or C₁-C₆-halogenoalkoxy-substituted phenyl;
   represents optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- and/or C₁-C₆-halogenoalkoxy-substituted phenyl-C₁-C₆-alkyl,
   represents in each case optionally halogen- and/or C₁-C₆-alkyl-substituted pyridyl, pyrimidyl, thiazolyl and pyrazolyl,
   or represents optionally halogen- and/or C₁-C₆-alkyl-substituted phenoxy-C₁-C₆-alkyl,

   R²

   represents in each case optionally halogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl, C₁-C₈-polyalkoxy-C₂-C₈-alkyl,
   represents in each case optionally halogen-, nitro-, C₁-C₆-alkyl, C₁-C₆-alkoxy- and/or C₁-C₆-halogenoalkyl-substituted phenyl or benzyl,

   R³, R⁴ and R⁵

   independently of one another each represent in each case optionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylamino, di-(C₁-C₈)-alkylamino, C₁-C₈-alkylthio, C₂-C₅-alkenylthio, C₂-C₅-alkinyl-thio, C₃-C₇-cycloalkylthio, represent in each case optionally halogen-, nitro-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-, C₁-C₄-alkyl- and/or C₁-C₄-halogenoalkyl-substituted phenyl, phenoxy or phenylthio,

   R⁶ and R⁷

   independently of one another each represent in each case optionally halogen-substituted C₁-C₂₀-alkyl, C₁-C₂₀-alkoxy, C₂-C₈-alkenyl, C₁-C₂₀-alkoxy-C₁-C₂₀-alkyl, represent in each case optionally halogen-, C₁-C₂₀-halogenoalkyl-, C₁-C₂₀-alkyl-or C₁-C₂₀-alkoxy-substituted phenyl, represent in each case optionally halogen-, C₁-C₂₀-alkyl-, C₁-C₂₀-halogenoalkyl- or C₁-C₂₀-alkoxy-substituted benzyl or together represent a C₂-C₆-alkylene ring which is optionally interrupted by oxygen,

   and at least one agonist or antagonist of nicotinic acetylcholine receptors.
2. Composition, comprising a synergistically effective mixture of compounds of the formula (I) according to Claim 1,
   in which

   X'

   represents C₁-C₄-alkyl, halogen, C₁-C₄-alkoxy or C₁-C₂-halogenoalkyl,

   Y'

   represents hydrogen, C₁-C₄-alkyl, halogen, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,

   Z'

   represents C₁-C₄-alkyl, halogen, C₁-C₄-alkoxy,

   n

   represents 0 or 1,

   A' and B'

   together with the carbon atom to which they are attached form a saturated 5- to 6-membered ring which is optionally substituted by C₁-C₄-alkyl and/or C₁-C₄-alkoxy,

   G'

   represents hydrogen (a) or represents the groups

   

   in which

   R¹

   represents in each case optionally halogen-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₂-C₆-alkyl or cycloalkyl having 3-7 ring atoms which may be interrupted by 1 to 2 oxygen and/or sulphur atoms,
   represents optionally halogen-, nitro-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl-and/or C₁-C₃-halogenoalkoxy-substituted phenyl;

   R²

   represents in each case optionally halogen-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl or C₁-C₆-alkoxy-C₂-C₆-alkyl,
   represents in each optionally halogen-, nitro-, C₁-C₄-alkyl-, C₁-C₄-alkoxy- and/or C₁-C₄-halogenoalkyl-substituted phenyl or ben-zyl,

   and at least one agonist or antagonist of nicotinic acetylcholine receptors.
3. Composition, comprising a synergistically effective mixture of the compound of the formula (Ia)

   

   and at least one agonist or antagonist of nicotinic acetylcholine receptors.
4. Composition according to any of Claims 1, 2 and 3, comprising compounds of the formula (I) and the agonist or antagonist of nicotinic acetylcholine receptors in a ratio of from 1:100 to 100:1.
5. Use of a synergistically effective mixture, comprising compounds of the formula (I) according to any of Claims 1, 2 and 3, and at least one agonist or antagonist of nicotinic acetylcholine receptors, for controlling animal pests.
6. Method for controlling animal pests, characterized in that mixtures as defined in any of Claims 1, 2 and 3 are allowed to act on animal pests and/or their habitat.
7. Process for preparing pesticides, characterized in that a synergistially effective amount comprising compounds of the formula (I) according to any of Claims 1, 2 and 3 and at least one agonist or antagonist of nicotinic acetylcholine receptors is mixed with extenders and/or surfactants.
8. Mixtures according to any of Claims 1, 2, 3 and 4, comprising at least one of the following compounds

   

   

   or

   

   or

   

   or